7-[(1R,2S,3R,5R)-5-chloro-2-formyl-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl]heptanoic acid methyl ester | 255721-48-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 7-[(1R,2S,3R,5R)-5-chloro-2-formyl-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl]heptanoic acid methyl ester
• 英文别名: 7-[(1α,2β,3α,5β)-2-Formyl-3-tetrahydropyranyloxy-5-chlorocyclopentyl]heptanoic acid methyl ester；methyl 7-[(1R,2R,3R,5R)-5-chloro-2-formyl-3-(oxan-2-yloxy)cyclopentyl]heptanoate
• CAS: 255721-48-3
• 化学式: C₁₉H₃₁ClO₅
• 分子量: 374.905
• InChiKey: JMVHXZWEHMBKRV-ROYKXYEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-[(1R,2S,3R,5R)-5-chloro-2-formyl-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl]heptanoic acid methyl ester 在 sodium hydroxide 、 正丁基锂 、 三甲基氯硅烷 、 对甲苯磺酸 、 magnesium 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 水 为溶剂， 生成 7-{(1R,2R,3R,5R)-5-Chloro-2-[(E)-(S)-4-(1-ethyl-cyclobutyl)-4-hydroxy-but-1-enyl]-3-hydroxy-cyclopentyl}-heptanoic acid
  参考文献：
  名称：

  A Practical Synthesis and Biological Evaluation of 9-Halogenated PGF Analogues

  摘要：

  A series of 9-halo PGF analogues 1-2 and 5-13 were synthesized and biologically evaluated. Among the compounds, 2 was the best EP2-receptor agonist. A practical method of synthesizing 2 via the Julia olefination of an aldehyde 3 with an optically active sulfone 4, which was prepared by Sharpless asymmetric epoxidation of 15, was developed. Other 9-halogenated PGF analogues were synthesized essentially by the same procedure and evaluated. The absolute configuration of 16-OH of 2 was determined as S by the X-ray analysis of a salt consisting of a 1/1 molar ratio of 2 and L-lysine. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00008-1
• 作为产物：
  描述：

  7-[(1R,2S,3R,5R)-5-chloro-2-hydroxymethyl-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl]heptanoic acid methyl ester 在 sodium chloride 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 生成 7-[(1R,2S,3R,5R)-5-chloro-2-formyl-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl]heptanoic acid methyl ester
  参考文献：
  名称：

  &ohgr;-cycloalkyl-prostaglandin E1 derivatives

  摘要：

  其中R1为OH等；X为Cl，F；R2为H，C1-8烷基，C2-8烯基，C2-8炔基，可能被取代；n为0-4。其非毒性盐或环糊精包合物能够强烈结合EP2亚型受体。因此，它们对于预防和/或治疗免疫性疾病（自身免疫疾病，移植后移植物排斥等），哮喘，异常骨骼形成，神经细胞死亡，肝病，流产，早产或视网膜神经病变（如青光眼）等是有用的。

  公开号：

  US06235780B1

文献信息

• &ohgr;-cycloalkyl-prostaglandin E1 derivatives
  申请人：Ono Pharmaceutical Co., Ltd.

  公开号：US06235780B1

  公开（公告）日：2001-05-22

  (wherein R1 is OH etc.; X is Cl, F; R2 is H, C1-8 alkyl, C2-8 alkenyl, C2-8 alkynyl which may be substituted; n is 0-4.), non-toxic salts thereof or cyclodextrin clathrates thereof can strongly bind on EP2 subtype receptor. Therefore, they are useful for the prevention and/or treatment of immunological diseases (autoimmune diseases, post-transplantation graft rejection etc.), asthma, abnormal bone formation, neuronal cell death, hepatopathy, abortion, premature birth or retina neuropathy (e.g. glaucoma) etc.

  其中R1为OH等；X为Cl，F；R2为H，C1-8烷基，C2-8烯基，C2-8炔基，可能被取代；n为0-4。其非毒性盐或环糊精包合物能够强烈结合EP2亚型受体。因此，它们对于预防和/或治疗免疫性疾病（自身免疫疾病，移植后移植物排斥等），哮喘，异常骨骼形成，神经细胞死亡，肝病，流产，早产或视网膜神经病变（如青光眼）等是有用的。
• A Practical Synthesis and Biological Evaluation of 9-Halogenated PGF Analogues
  作者：K Tani

  DOI：10.1016/s0968-0896(02)00008-1

  日期：2002.6

  A series of 9-halo PGF analogues 1-2 and 5-13 were synthesized and biologically evaluated. Among the compounds, 2 was the best EP2-receptor agonist. A practical method of synthesizing 2 via the Julia olefination of an aldehyde 3 with an optically active sulfone 4, which was prepared by Sharpless asymmetric epoxidation of 15, was developed. Other 9-halogenated PGF analogues were synthesized essentially by the same procedure and evaluated. The absolute configuration of 16-OH of 2 was determined as S by the X-ray analysis of a salt consisting of a 1/1 molar ratio of 2 and L-lysine. (C) 2002 Elsevier Science Ltd. All rights reserved.